(S)-2-Methyl-7-octene-2,3-diol | 146886-26-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-Methyl-7-octene-2,3-diol
• 英文别名: (3S)-2-methyloct-7-ene-2,3-diol
• CAS: 146886-26-2
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: OARWWPOYLBAZGD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-Methyl-7-octene-2,3-diol 在 吡啶 、 IR 120 H⁺-form 、 臭氧 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 (S)-5-Hexyl-2,2,4,4-tetramethyl-[1,3]dioxolane
  参考文献：
  名称：

  Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes

  摘要：

  Asymmetric biohydrolysis of trialkyl oxiranes (+/-)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols Ib 3b in Lip to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence vas investigated by O-18-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00256-7
• 作为产物：
  描述：

  7-甲基-1，6-辛二烯 在 硫酸 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-2-Methyl-7-octene-2,3-diol
  参考文献：
  名称：

  Asymmetric Total Synthesis of a Beer-Aroma Constituent Based on Enantioconvergent Biocatalytic Hydrolysis of Trisubstituted Epoxides

  摘要：

  植物成分月桂烯二醇 [(R)-1] 和 (S)-7,7-二甲基-6,8-二氧杂双环[3.2.1]辛烷 (2)（一种挥发性成分）的简短不对称全合成啤酒的香气是通过化学酶协议实现的。关键步骤包括带有烯属侧链的三取代环氧化物的生物催化水解，该水解以对映体聚合方式进行，即从外消旋物中获得单一对映体vic-二醇，其ee率高达91%，分离产率高达92%。

  DOI：

  10.1055/s-2001-17713

文献信息

• New Ligands and Improved Enantioselectivities for the Asymmetric Dihydroxylation of Olefins
  作者：Heinrich Becker、S. Bruce King、Masahiko Taniguchi、Koenraad P. M. Vanhessche、K. Barry Sharpless

  DOI：10.1021/jo00118a005

  日期：1995.6
• Biocatalytic asymmetric and enantioconvergent hydrolysis of trisubstituted oxiranes
  作者：Andreas Steinreiber、Sandra F. Mayer、Robert Saf、Kurt Faber

  DOI：10.1016/s0957-4166(01)00256-7

  日期：2001.6

  Asymmetric biohydrolysis of trialkyl oxiranes (+/-)-1a-3a using the epoxide hydrolase activity of whole bacterial cells proceeded in an enantioconvergent fashion and thus led to the corresponding (R)-configurated vicinal diols Ib 3b in Lip to 97% enantiomeric excess (e.e.) as the sole product. The mechanism of this enantioconvergence vas investigated by O-18-labelling experiments and it was found that both enantiomers were hydrolysed with opposite regioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric Total Synthesis of a Beer-Aroma Constituent Based on Enantioconvergent Biocatalytic Hydrolysis of Trisubstituted Epoxides
  作者：Andreas Steinreiber、Sandra F. Mayer、Kurt Faber

  DOI：10.1055/s-2001-17713

  日期：——

  A short asymmetric total synthesis of the plant constituent myrcenediol [(R)-1], and (S)-7,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane (2), which is a volatile constituent of the aroma of beer was accomplished via a chemoenzymatic protocol. The key step consisted of a biocatalytic hydrolysis of trisubstituted epoxides bearing olefinic side chains which proceeded in an enantioconvergent fashion, i.e., a single enantiomeric vic-diol was obtained from the racemate in up to 91% ee and 92% isolated yield.

  植物成分月桂烯二醇 [(R)-1] 和 (S)-7,7-二甲基-6,8-二氧杂双环[3.2.1]辛烷 (2)（一种挥发性成分）的简短不对称全合成啤酒的香气是通过化学酶协议实现的。关键步骤包括带有烯属侧链的三取代环氧化物的生物催化水解，该水解以对映体聚合方式进行，即从外消旋物中获得单一对映体vic-二醇，其ee率高达91%，分离产率高达92%。